Functional Groups 2 Flashcards
Synthesis of Dienes
- ) dehydration of diols
- ) dehydrogenation of alkenes
- ) dehydrohalogenation of dihalides
Dehydration of diols
HOCH2CH2CH2CH2OH
-H2SO4-> CH2=CH-CH=CH2
Dehydrohalogenation of dihalides
CH3CHXCH2CH2X
-strong base/heat->
CH2=CH-CH=CH2
Reaction of dienes
- ) addition of hydrogen
2. ) Diels-Alder reaction
Preparation of alkyl halides
- ) alcohol + HX
- ) alcohol + PX3
- ) addition of HX to alkenes
- ) halogenation of alkanes with Cl2 or Br2
Reactions of alkyl halides
- ) synthesis oh higher alkanes
- ) synthesis of R-OH using NaOH
- ) elimination
- ) synthesis of Grignard reagents
Formaldehyde (H2C=O) + GR (react with H2O in 2nd step)
Primary alcohol
Aldehyde + GR (react with H2O in 2nd step)
Secondary alcohol
Ketone + GR (react with H2O in 2nd step)
Tertiary alcohol
Nitrile + GR (react with H2O in 2nd step)
Ketone
Cabon Dioxide + GR (react with HCl in 2nd step)
Carboxylic acid
When to ad -ok to an alcohol
When alcohols have double and triple C-C bonds, add -ok to the end to specify and alcohol; lowest carbon number goes to carbon with -OH
Synthesis of alcohols
- ) Hydration of Alkenes
- ) hydrolysis of alkyl halides
- ) preparation from Grignard reagents
- ) oxymercuration-demercuration of Alkenes
- ) hydroboration-oxidation of Alkenes
Oxidation of primary alcohols to carboxylic acids
RCH2OH -Na2Cr2O7,H2SO4-> RCOOH
Oxidation of primary alcohols to aldehydes
RCH2OH -CrO3,PCC-> RCHO
Oxidation of secondary alcohols to ketones
R-CH(OH)-R’ -Na2Cr2O7,H2SO4-> R-CO-R’
Reduction of alcohols to alkanes
ROH -LiAlH4,TiCl4-> R-H
Synthesis of alkyl halides
ROH + HX -> RX
Dehydration of Alkenes
CH3CH2OH -acid,heat-> H2C=CH2 + H2O
Dehydration to ethers
2ROH + acid ->R-O-R + H2O
Tosylation
ROH + tosyl chloride -pyridine(PCC)-> alkyl tosylate
Acylation
ROH + ClCOR’ (acyl chloride) -> OR-COR’ (ester)
Deprotonation to alkoxide
R-OH + Na -> R-O^- Na^+
Or
R-OH + K -> R-O^- K^+
Thiols
Have -SH groups
